Best 188 things to do in Longboat Key, FL

Private double-decker party boat in Bradenton Beach with slide and BYOB cruising

Private Anna Maria Island sunset cruise for up to 12 guests

Enjoy a self-guided paddle adventure with a versatile inflatable board.

Cruise Anna Maria Island by captained tritoon with room for up to 6

Customize your route with snorkeling, sightseeing, and island stops on a private boat

Customize a private Anna Maria & Long Boat Key boat tour for up to 6 people

Customize a 3-hour beach picnic with setup and cleanup included

Reserve a beach suite setup for six, ready from 10am–4pm

Set up a 3-hour sunset beach picnic for two

Cruise to a local sandbar and swim or snorkel

Cruise the Gulf and back bay to look for dolphins and seasonal manatees

Cruise into the evening and watch the sunset from the water

Experience marine life up close on a comfortable pontoon cruise for all ages.

Cruise Sarasota Bay to Big Pass for Gulf sunset views

Private 6–8 hour Bali 4.2 catamaran charter on Sarasota Bay

Enjoy a customizable luxury sail with captain and mate aboard a spacious 42-ft catamaran.

Charter a 38-foot Sea Ray for 6 hours of Sarasota Bay cruising

Charter a 38-foot Sea Ray for a 4-hour Sarasota Bay cruise

Book a 3- or 4-hour private sunset cruise on a 38-foot Sea Ray

Private sunset cruise on Kai Fin with premium seating and water toys

Fish offshore with a USCG-licensed captain, mate, bait, and standard fuel included

Charter the 50' Memory Maker for 3 hours with four lounge areas

A custom chef‑curated feast celebrating bold local flavors and dietary wellness—served right in your home or rental

Pedal kayak Sarasota Bay to seagrass beds and mangrove tunnels